So I played a boss rush without any mountables only SSH skill, CI4 background and CI5 boss theme and I finished it but game won’t give me extreme unpreparedness. I can only get it by equipping literally nothing.
I have, like, over seventy of these medals (from memory) and @ScarletCuboids is right that before 40.2 this wouldn’t have been an issue - skills, backgrounds, and music never triggered it previously (and it is silly that any of them would, in my opinion) so this qualifies as a bug in my opinion.
EDIT: Just did some testing, can confirm this is an issue only with the “Boss Music” slot